Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
  • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
  • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
  • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
  • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
  • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
  • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
  • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
  • C09B62/443—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being alternatively specified
  • C09B62/447—Azo dyes
  • C09B62/45—Monoazo dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
  • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
  • C09B62/523—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl amido or hydroxyalkyl amino sulfonyl group, a quaternised or non-quaternised amino alkyl sulfonyl amido group, or a substituted alkyl amino sulfonyl group, or a halogen alkyl sulfonyl amido or halogen alkyl amino sulfonyl group or a vinyl sulfonylamido or a substituted vinyl sulfonamido group
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
  • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
  • C09B62/523—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl amido or hydroxyalkyl amino sulfonyl group, a quaternised or non-quaternised amino alkyl sulfonyl amido group, or a substituted alkyl amino sulfonyl group, or a halogen alkyl sulfonyl amido or halogen alkyl amino sulfonyl group or a vinyl sulfonylamido or a substituted vinyl sulfonamido group
  • C09B62/527—Azo dyes
  • C09B62/53—Monoazo dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
  • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
  • C09B62/62—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an ethylenimino or N—acylated ethylenimino group or a —CO—NH—CH2—CH2—X group, wherein X is a halogen atom, a quaternary ammonium group or O—acyl and acyl is derived from an organic or inorganic acid, or a beta—substituted ethylamine group
  • C09B62/66—Azo dyes

Definitions

• This invention provides valuable new azo-dyestutis, which contain an acid group imparting solubility in water but contain no N-acylated sulfonic acid amide groups, and also contain a group of the formula in which R represents an alkylene radical which may contain substituents, Z represents the radical of an organic sulfonic acid bound through an oxygen atom of its functional group to R, and n represents a whole number not greater than 2.
• the dystulfs of this invention which contain a group of the Formula 1, in which Z represents the radical of an aliphatic or aromatic sulfonic acid.
• the dyestuffs of this invention contain an acid group imparting solubility in water such, for example, as a -SO2NH2 group, a sulfone group, for example a methylsulfone group, a
• caiboxyl group or advantageously a sulfonic acid group
• the acid group imparting solubility and the group of the Formula 1 may be present in the dyestutf molecule in any desired positions, that is to say, a group of eachkind may be present in the radical of a single component or one dyestuif component may contain, for example, the group imparting solubility, and the other component may contain the group of the Formula 1.
• a group of eachkind may be present in the radical of a single component or one dyestuif component may contain, for example, the group imparting solubility, and the other component may contain the group of the Formula 1.
• monoazo-dyestuifs of the latter kind which contain the group of the Formula 1 in the radical of the diazo component and the acid group imparting solubility in the radical of the coupling component.
• dyestuffs of the invention there are advantageously used dyestutf components which alreadycontain the aforesaid groups.
• the dyestuff components to be used may, of course, contain other substituents such, for example, as halogen atoms, nitro groups, acylamino groups, alkyl groups or alkoxy groups.
• diazo compounds which contain no hydroxyl group in ortho-position to the diazo group.
• B Components containing an acid group imparting solubility of the kind mentioned above, such as diazo compounds of 1-arninobenzene-3- or -4-sulfonic acid amide, 1-aminobenzene-2, -3- or -4-methyl sulfone, l-aminobenzene-2 -3- or -4-sulfonic acid, Z-methylor 2-methoxy-1- aminobenzene-4- or -5sulfonic-acid, Z-aminonaphthalene- 6-sulfonic acid, .and the following coupling components: 1-.hydroxynaphthalene-4- or -5-sulfonic acid, 2-hydroxynaphthalene-3-, -4:, -'5-, -'6-, -'7- or 8- sulfonic acid, 2:9- dihydroxynaphtha1ene-6-sulfonic acid, Z-aminonaphthalene-6-sulfonic acid, Z-amino
• the monoazo-dyestufls obtainable from the foregoing components by coupling a diazo compound mentioned under B with a coupling component mentioned under A or above all by coupling a diazo compound under A with a coupling component under B in a not strongly alkaline, and advantageously neutral to acid, medium, are new.
• azo-dyestufis which contain at least one acid group imparting solubility, but no N-acylated sulfonic acid amide group, and a group of the above Formula 1.
• RTN N-PZ SOz-(NH),.-1(CHz)m-OSO -Z in which R represents the radical of a diazo-component of the naphthalene or advantageously benzene series, Z represents .an aliphatic or aromatic radical, m represents them/hole number 2 or 3, 11 represents a whole number not greater than 2, and Pz represents a 5-pyrazo1one radical which contains in the 3- or advantageously 1- position an aryl radical containing a sulfonic acid group as a substituent.
• the dyestufis can be used for dyeing or printing a very wide variety vof materials especially nitrogenous natural or artificial 'fibers such as leather, silk, wool and structures of superpolyamides or superpolyurethanes. They are suitable for dyeing from a weakly acid to approximately neutral bath.
• the dyeings -.so obtained are uniform and are distinguished by their good fastness to light and their excellent fastness to washing, fulling and alkali.
• the resulting dyestuif of the formula fochloride in pyridine followed by acid splitting of the acetylarnino group are diazotized as described in Example l, and coupled with a solution of 26 parts of 1- phenyl-3-methyl-5 pyrazolone 3'-sulfonic acid and 30 parts of crystalline sodium acetate in 250 parts of water.
• the dyestufi which in form of its sodium salt corresponds to N-O-SOIINB.
• Example 2 40 parts of l-methoxy-Z-aminobenzene-4-sulfonic acid- N- 8-(para toluene sulfonyloxy) ethylamide (prepared from 1-methoXy-2-acetylaminobenzene 4 sulfonic acid- N-p-hydroxyethylamide by reaction with paratoluene sul- OH is salted out with sodium chloride, filtered and dried. 15 1116 formula The new dyestufi, an orange-red powder, dissolves in water a red-yellow coloration and dyes wool from a Weakly acid bath pure yellow tints of excellent fastness to washing, fulling and light.
• Diazoeomponent Coupling component (EH OH 6 -r BOrN'Ef6H1CHlO -SO:OOH
• the 2-aminonaphthalene--sulfonic acid ,8-(tosyloxy)-ethylamide necessary for making dyestufi No. 8 of the above table can be prepared, for example, by treating Z-acetylamino naphthalene-6-sulfonic acid-fi-hydroxyethylamide in pyridine with para-toluene sulfochloride, pouring the reaction mixture into ice water, and hydrolyzing the acetyl group in the resulting reaction product with dilute hydrochloric acid with the aid of heat.
• Example 3 0.5 part of the dyestufi obtainable as described in Example 1 is dissolved in 4000 parts of water, 10 parts Of crystalline sodium sulfate are added, and 100 parts of well wetted wool are entered into the resulting dyebath at -50" C. 2 parts of acetic acid of 40 percent strength are then added, the temperature is raised to the boil in the course of /2 hour, and dyeing is carried on at the boil for hour. Finally the wool is rinsed with cold water and dried. There is obtained a level yellow dyeing of good fastness to light and excellent fastness to washing.
• a level yellow dyeing of good fastness to light and excellent fastness to washing is also obtained by proceeding in the manner described above, but without the addition of acetic acid to the dyebath.
• a monoazo dyestufi which in its free acid form corresponds to the formula Hahn-O-SOr-R:
• R, R1 and R2 each represents a benzene radical, and m represents a whole number up to 2.
• a monoazo dyestufi which in its free acid form corresponds to the formula wherein m, n and p each represents a whole number up to two, X and Y each represents a member selected from the group consisting of a chlorine and a hydrogen atom.
• the monoazo dyestuif which in its free acid form corresponds to the formula 4.
• the monoazo dyestufi whichin its free and form corresponds to the formula corresponds to the formula 01 H H0 t, 0H: 77 I v OCH; GN

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• Inorganic Chemistry (AREA)
• Coloring (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 0
  • BE BE534436D patent/BE534436A/fr unknown
• 1953
  • 1953-12-28 CH CH333923D patent/CH333923A/de unknown
• 1954
  • 1954-12-21 DE DE1954C0010462 patent/DE1002099C2/de not_active Expired
  • 1954-12-22 FR FR1116358D patent/FR1116358A/fr not_active Expired
  • 1954-12-27 US US477933A patent/US2799672A/en not_active Expired - Lifetime
  • 1954-12-28 GB GB37497/54A patent/GB774819A/en not_active Expired

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